EP2172118A2 - Compositions fluides contenant des polyphénols et leur procédé de préparation et d'emballage - Google Patents

Compositions fluides contenant des polyphénols et leur procédé de préparation et d'emballage Download PDF

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Publication number
EP2172118A2
EP2172118A2 EP09162642A EP09162642A EP2172118A2 EP 2172118 A2 EP2172118 A2 EP 2172118A2 EP 09162642 A EP09162642 A EP 09162642A EP 09162642 A EP09162642 A EP 09162642A EP 2172118 A2 EP2172118 A2 EP 2172118A2
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EP
European Patent Office
Prior art keywords
resveratrol
trans
alcoholic
retail
beverage
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09162642A
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German (de)
English (en)
Other versions
EP2172118A3 (fr
Inventor
Frederick Feller, Iii
Jay S. Yadav
Gregory Lamps
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IdeaMed LLC
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IdeaMed LLC
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Filing date
Publication date
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Publication of EP2172118A2 publication Critical patent/EP2172118A2/fr
Publication of EP2172118A3 publication Critical patent/EP2172118A3/fr
Withdrawn legal-status Critical Current

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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B65CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65DCONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D51/00Closures not otherwise provided for
    • B65D51/24Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes
    • B65D51/28Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials
    • B65D51/2807Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials the closure presenting means for placing the additional articles or materials in contact with the main contents by acting on a part of the closure without removing the closure, e.g. by pushing down, pulling up, rotating or turning a part of the closure, or upon initial opening of the container
    • B65D51/2814Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials the closure presenting means for placing the additional articles or materials in contact with the main contents by acting on a part of the closure without removing the closure, e.g. by pushing down, pulling up, rotating or turning a part of the closure, or upon initial opening of the container the additional article or materials being released by piercing, cutting or tearing an element enclosing it
    • B65D51/2828Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials the closure presenting means for placing the additional articles or materials in contact with the main contents by acting on a part of the closure without removing the closure, e.g. by pushing down, pulling up, rotating or turning a part of the closure, or upon initial opening of the container the additional article or materials being released by piercing, cutting or tearing an element enclosing it said element being a film or a foil
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52Adding ingredients
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to compositions comprising polyphenols and, in particular, to compositions comprising resveratrol.
  • Trans-resveratrol and other naturally occurring polyphenols are believed to have a number of potential health benefits. Such benefits include protective effects against cardiovascular disease, neurodegeneration, and cancer. Trans-resveratrol and other plant phenols have also been shown to stimulate SIRT1, a sirtuin enzyme. It has been reported that increasing the activity level of SIRT1 increases life spans in a diversity of organisms.
  • Trans-resveratrol is reported to occur in European red wines in amounts on the order of 0.5-5 mg/L. Additionally, pinot noir wines from the New York region are reported to contain up to 10 mg/L of trans-resveratrol. Moreover, trans-resveratrol quantities in non-alcoholic red wines are reported to be less than 4 mg/L.
  • red wines include trans-piceattanol, fisetin, luteolin, kaempferol, quercetin, apigenin, naringenin, (+)-catechin, (-)-epicatechin, morin, and cis-resveratrol.
  • red wines may be unattractive to some groups of individuals due to its alcohol content.
  • groups of individuals can include people who are taking medications for which alcohol consumption is contraindicated, individuals that suffer from alcohol dependencies, people who suffer from depression, pregnant mothers, adolescents, and people that abstain from alcohol consumption as part of their preferred lifestyle.
  • the polyphenol content of non-alcoholic beverages is significantly less than that of alcoholic beverages.
  • the solubility and stability of polyphenols, specifically trans-resveratrol, in non-alcoholic, non-fermented aqueous solutions at concentrations comparable to quantities present in red wine have not been realized.
  • the present invention provides a number of compositions, including non-alcoholic and non-fermented aqueous solutions comprising trans-resveratrol and/or other polyphenols.
  • the present invention provides retail or commercially available beverages comprising trans-resveratrol and/or other polyphenols.
  • the present invention additionally provides packaging operable to maintain the stability of trans-resveratrol in an alcohol-free, aqueous solution.
  • the packaging may also be operable to maintain an acceptable level of trans-resveratrol stability between the time ofpackaging and the time of consumption or use of the trans-resveratrol solution.
  • the present invention provides methods of producing aqueous solutions and/or retail beverages comprising trans-resveratrol as well as methods of increasing the solubility of trans-resveratrol in aqueous solution.
  • the present invention provides a number of compositions, including non-alcoholic and/or non-fermented aqueous solutions comprising trans-resveratrol and/or other polyphenols.
  • the present invention provides a fluid composition comprising an aqueous solution comprising trans-resveratrol in an amount greater than 30 mg/L.
  • an aqueous solution comprises trans-resveratrol in an amount ranging from greater than 30 mg/L up to about 300 mg/L.
  • an aqueous solution comprises trans-resveratrol in an amount ranging from about 50 mg/L to about 200 mg/L or from about 100 mg/L to about 150 mg/L.
  • an aqueous solution comprises trans-resveratrol in an amount greater than about 300 mg/L.
  • a fluid composition comprises an aqueous solution comprising trans-resveratrol in an amount greater than 5 mg/L to about 30 mg/L.
  • an aqueous solution comprising trans-resveratrol in any of the amounts provided herein comprises ethanol in an amount less than about 5 percent by volume. In other embodiments, an aqueous solution comprises ethanol in an amount less than about 2 percent by volume. In another embodiment, an aqueous solution comprising trans-resveratrol in any of the amounts recited herein comprises ethanol in an amount less than about 1 percent by volume. In a further embodiment, an aqueous solution comprises ethanol in an amount less than about 0.5 percent by volume. In one embodiment, an aqueous solution comprising trans-resveratrol in any of the amounts provided herein does not comprise ethanol and/or other alcohol(s).
  • an aqueous solution comprising trans-resveratrol in any of the amounts provided herein further comprises at least one stabilizing agent.
  • an aqueous solution comprises a plurality of stabilizing agents.
  • Stabilizing agents comprise chemical species operable to enhance the stability of trans-resveratrol in aqueous solution by inhibiting or preventing the geometric isomerization of trans-resveratrol to the cis-isomer.
  • stabilizing agents minimize and/or eliminate elements or species that facilitate the conversion of trans-resveratrol to cis-resveratrol.
  • stabilizing agents comprise nitrogen, carbon dioxide, or mixtures thereof. In other embodiments, stabilizing agents comprise vitamin A, vitamin C, vitamin E, or mixtures thereof. In some embodiments, an aqueous solution comprising trans-resveratrol comprises vitamin C in an amount of up to about 1000 mg/L. In another embodiment, an aqueous solution comprising trans-resveratrol comprises vitamin A in an amount ranging from about 1 to about 6,250 International Units (IU's) or from about 2,100 IU's to about 4,200 IU's. In a further embodiment, an aqueous solution comprising trans-resveratrol comprises vitamin E in an amount ranging from about 1 to about 125 IU's or from about 12.5 to about 125 IU's.
  • IU's International Units
  • an aqueous solution comprising trans-resveratrol comprises vitamin E in an amount ranging from about 1 to about 125 IU's or from about 12.5 to about 125 IU's.
  • an aqueous solution in some embodiments of the present invention, can comprise trans-resveratrol in any amount recited herein for a time period of at least six months from the preparation of the aqueous solution.
  • an aqueous solution comprises greater than 30 mg/L up to about 300 mg/L of trans-resveratrol at least six months after preparation of the aqueous solution.
  • an aqueous solution comprises trans-resveratrol in an amount greater than 5 mg/L to about 30 mg/L at least six months after preparation of the solution. In another embodiment, an aqueous solution comprises trans-resveratrol in any amount provided herein for a time period of at least 9 months after preparation of the solution.
  • an aqueous solution comprising trans-resveratrol in any of the amounts recited herein further comprises other polyphenols including, but not limited to, trans-piceattanol, fisetin, luteolin, kaempferol, quercetin, apigenin, naringenin, (+)-catechin, (-)-epicatechin, morin, and cis-resveratrol.
  • aqueous solutions comprising trans-resveratrol do not comprise cis-resveratrol.
  • emulsifying agents are employed to further enhance the dispersion of trans-resveratrol in aqueous solution.
  • Suitable emulsifying agents comprise calcium carbonate, lecithin, methylcellulose, mono- and diglycerides, pectin and phosphoric acid.
  • Aqueous solutions comprising trans-resveratrol in some embodiments, have a pH ranging from about 2.5 to about 7. In other embodiments, aqueous solutions comprising trans-resveratrol have a pH ranging from about 2.5 to about 4.5. In a further embodiment, aqueous solutions comprising trans-resveratrol have a pH ranging from about 3 to about 4.
  • the present invention provides retail beverages comprising trans-resveratrol.
  • the present invention provides a retail beverage comprising trans-resveratrol in an amount ranging from about 5 mg/L to about 300 mg/L, wherein the retail beverage is non-alcoholic.
  • non-alcoholic refers to an alcohol (ethanol) content of the beverage less than about 0.5% by volume.
  • a non-alcoholic retail beverage comprises trans-resveratrol in an amount ranging from about 10 mg/L to about 300 mg/L or from about 30 mg/L to about 250 mg/L.
  • a non-alcoholic retail beverage comprising trans-resveratrol in any of the amounts provided herein further comprises at least one stabilizing agent.
  • a non-alcoholic retail beverage comprises a plurality of stabilizing agents.
  • stabilizing agents for use in retail beverages comprising trans-resveratrol comprise vitamin A, vitamin C, vitamin E, or combinations thereof.
  • a non-alcoholic retail beverage comprising trans-resveratrol further comprises vitamin C in an amount of up to about 1000 mg/L.
  • a non-alcoholic retail beverage comprising trans-resveratrol further comprises vitamin A in an amount ranging from about 1 to about 6,250 IU's or from about 2,100 to about 4,200 IU's.
  • a non-alcoholic retail beverage comprising trans-resveratrol further comprises vitamin E in an amount ranging from about 1 to about 125 IU's or from about 12.5 to about 125 IU's.
  • stabilizing agents suitable for use in non-alcoholic retail beverages comprising trans-resveratrol comprise chemical species operable to absorb ultra-violet radiation.
  • a non-alcoholic retail beverage in some embodiments of the present invention, can comprise trans-resveratrol in any amount recited herein for a time period of at least six months from the preparation of the non-alcoholic retail beverage.
  • an aqueous solution comprises from about 5 mg/L up to about 300 mg/L of trans-resveratrol at least six months after the aqueous solution is prepared.
  • a non-alcoholic retail beverage comprises trans-resveratrol in an amount greater than 5 mg/L to about 30 mg/L at least six months after preparation of the non-alcoholic retail beverage. In another embodiment, a non-alcoholic retail beverage comprises trans-resveratrol in any amount provided herein for a time period of at least 9 months after preparation of the solution.
  • flavoring agents comprise methyl salicylate, allyl cyclohexylpropionate, citral, citronellal, citronellol, 1,8-cineole (eucalyptol), cinnamyl alcohol (cinnamic alcohol), cinnamaldehyde (cinnamic aldehyde), decanal (decyl aldehyde), decanol (decyl alcohol), ethyl dicanoate (ethyl caprate), terpineol, ⁇ -nonalactone (nonalactone), vanillin, p-methylacetophenone, hydroxycitonellal, hydroxycitronellal dimethylacetate, piperonal (heliotropine), isoamyl phenlacetate, isobutyl phenylacetate, ethyl penylacetate, propionic acid, isoamyl propionate, ethyl propionate, benz
  • flavoring agents comprise benzyl alcohol, benzaldehyde, d-bomeol, maltol, methyl N-methylanthranilate, methyl b-naphthyl ketone, dl- menthol (dl-peppermint camphor), l -menthol (peppermint camphor), butyric acid, isoamyl butylate, ethyl butyrate, cyclohexyl butyrate, butylrate, or linalool (linalol) or combinations thereof.
  • Non-alcoholic retail beverages comprising trans-resveratrol in some embodiments, have a pH ranging from about 3 to about 7. In other embodiments, non-alcoholic retail beverages comprising trans-resveratrol have a pH ranging from about 3.5 to 4.5.
  • a non-alcoholic retail beverage comprising trans-resveratrol has no calories.
  • a non-alcoholic retail beverage comprising trans-resveratrol has from about 1 to about 200 calories per serving.
  • a non-alcoholic retail beverage comprising trans-resveratrol has from about 10 to about 150 or from about 25 to about 100 calories per serving.
  • a non-alcoholic retail beverage comprising trans-resveratrol has from about 50 calories to about 75 calories per serving.
  • Non-alcoholic retail beverages comprising trans-resveratrol in any of the amounts recited herein, in some embodiments, are teas.
  • a non-alcoholic retail beverage comprising trans-resveratrol is an energy or sports drink operable to replenish electrolytes and/or carbohydrates.
  • a non-alcoholic retail beverage comprising trans-resveratrol is yogurt or a "smoothie" type fluid composition.
  • a non-alcoholic retail beverage comprising trans-resveratrol is a cola or other acidic carbonated soft drink.
  • Yet another embodiment of a non-alcoholic beverage comprising trans-resveratrol is coffee.
  • a retail alcoholic beverage comprises trans-resveratrol in an amount greater than 15 mg/L. In another embodiment, a retail alcoholic beverage comprises trans-resveratrol in an amount ranging from greater than about 15 mg/L to about 2.5 g/L. In some embodiments, a retail alcoholic beverage comprises trans-resveratrol in an amount ranging from about 20 mg/L to about 1 g/L or from about 50 mg/L to about 750 mg/L.
  • a retail alcoholic beverage comprising trans-resveratrol in any of the amounts recited herein is a beer or malt beverage.
  • a retail alcoholic beverage comprising trans-resveratrol in any of the amounts provided herein is a wine, wherein a wine comprises a white wine, a red wine, or a mixture thereof.
  • a retail alcoholic beverage comprising trans-resveratrol in any of the amounts provided herein is a liquor.
  • Retail alcoholic beverages comprising trans-resveratrol can further comprise any of the additional components provided herein for non-alcoholic retail beverages including, but not limited to, stabilizing agents, additional polyphenols, flavoring agents, and/or emulsifying agents.
  • retail alcoholic beverages comprising trans-resveratrol can have caloric contents consistent with those recited herein for non-alcoholic retail beverages.
  • an alcoholic retail beverage in some embodiments of the present invention, can comprise trans-resveratrol in any amount recited herein for a time period of at least six months from the preparation of the alcoholic retail beverage.
  • a retail alcoholic beverage comprises greater than 15 mg/L up to about 2.5 g/L of trans-resveratrol at least six months after the retail alcoholic beverage is prepared.
  • a retail alcoholic beverage comprises trans-resveratrol in an amount ranging from about 20 mg/L to about 750 mg/L at least six months after preparation of the retail alcoholic beverage.
  • a retail alcoholic beverage comprises trans-resveratrol in any amount provided herein for a time period of at least 9 months after preparation of the solution.
  • Retail alcoholic beverages are available for purchase at commercial outlets including, but not limited to, grocery stores, drug stores, convenience stores, health specialty stores, and/or alcohol beverage control establishments.
  • Trans-resveratrol for use in aqueous solutions, non-alcoholic retail beverages, and retail alcoholic beverages can be obtained from a synthesized source or, alternatively, as plant or natural food extract. Methods of trans-resveratrol synthesis and extraction are well known to those in the art. Extraction of trans-resveratrol, for example, can be obtained from grape seeds, grape skin, grape pumace, and Japanese Knotweed ( Polygonum cuspidatum ).
  • trans-resveratrol for use in aqueous solutions, non-alcoholic retail beverages, and retail alcoholic beverages of the present invention is in the 3- ⁇ -glucoside form of trans-resveratrol.
  • This form of trans-resveratrol is 2-[3-hydroxy-5-[( E )-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol, otherwise known as polydatin or piceid.
  • the bioavailability of the trans-resveratrol derived from the ⁇ -glucosidic form is equivalent to the free form of trans-resveratrol in solution.
  • Concentrations of piceid in aqueous solutions, retail non-alcoholic, and retail alcoholic beverages of the present invention are determined such that the quantity of free trans-resveratrol released upon hydrolysis remains within the trans-resveratrol ranges set forth herein.
  • the present invention provides packaging for aqueous solutions, non-alcoholic retail beverages, and retail alcoholic beverages comprising trans-resveratrol operable to enhance the stability of trans-resveratrol in solution by inhibiting geometric isomerization to cis-resveratrol.
  • Aqueous solutions and retail beverages disclosed herein comprising trans-resveratrol can be contained within and protected from exposure to UV radiation by a plastic bottle material, e.g., specific grades of polyethylene terephthalate (PET) well known to those in the art, which have specialized additives for blocking a specific range ofUV wavelengths while maintaining a "clear" bottle appearance.
  • a plastic bottle material e.g., specific grades of polyethylene terephthalate (PET) well known to those in the art, which have specialized additives for blocking a specific range ofUV wavelengths while maintaining a "clear" bottle appearance.
  • colorants can also be added to the plastic or glass bottling material to provide further protection of the contents against UV-degradation. These additives may block or absorb UV light in certain wavelengths.
  • aqueous solutions and/or retail beverages of the present invention are packaged in cans including, but not limited to, aluminum cans, steel cans with a polymeric film liner, or multi-layer aseptic paper/plastic packaging such as packaging commercially available from Tetra Pak of Switzerland.
  • Trans-resveratrol + ascorbic acid 100 ml of water was heated to about 90°C in a glass beaker. 6 mg of trans-resveratrol extract (99%, Abatra Lot #0606231) was added to the heated water with a hand blender to produce a solution having a trans-resveratrol concentration of 60 mg/L. 600 mg of ascorbic acid (powder) L-ascorbic acid (powder) from BDH, distributed exclusively for VWR, 99.7% pure, lot #45335635, was added to the trans-resveratrol solution with mild stirring to produce an ascorbic acid concentration of 6 g/L.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Mechanical Engineering (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Packging For Living Organisms, Food Or Medicinal Products That Are Sensitive To Environmental Conditiond (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Wrappers (AREA)
EP09162642A 2006-06-13 2007-06-13 Compositions fluides contenant des polyphénols et leur procédé de préparation et d'emballage Withdrawn EP2172118A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81314706P 2006-06-13 2006-06-13
EP07796042A EP2035538A2 (fr) 2006-06-13 2007-06-13 Formules de fluides comprenant des polyphénols et méthodes de fabrication et d'emballage desdites formules

Related Parent Applications (2)

Application Number Title Priority Date Filing Date
WOPCT/US2007/013842 Previously-Filed-Application 2007-06-13
EP07796042.5 Division 2007-06-13

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EP2172118A2 true EP2172118A2 (fr) 2010-04-07
EP2172118A3 EP2172118A3 (fr) 2011-09-07

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EP09162642A Withdrawn EP2172118A3 (fr) 2006-06-13 2007-06-13 Compositions fluides contenant des polyphénols et leur procédé de préparation et d'emballage
EP07796042A Withdrawn EP2035538A2 (fr) 2006-06-13 2007-06-13 Formules de fluides comprenant des polyphénols et méthodes de fabrication et d'emballage desdites formules

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EP07796042A Withdrawn EP2035538A2 (fr) 2006-06-13 2007-06-13 Formules de fluides comprenant des polyphénols et méthodes de fabrication et d'emballage desdites formules

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US (1) US20080213433A1 (fr)
EP (2) EP2172118A3 (fr)
WO (1) WO2007146318A2 (fr)

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CA2711734A1 (fr) 2008-01-08 2009-07-16 David Rubin Compositions et procede d'administration de resveratrol et de pterostilbene
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WO2010138584A1 (fr) * 2009-05-27 2010-12-02 Cliff Oster Produit de type boisson contenant du resvératrol
CA2769278A1 (fr) * 2009-08-10 2011-02-17 Stokely-Van Camp, Inc. Procede pour mettre un flavonoide en suspension dans une boisson
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WO2013183177A1 (fr) * 2012-06-07 2013-12-12 株式会社燦樹 Composition de jaune d'œuf à l'ail et son procédé de production
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WO2007146318A2 (fr) 2007-12-21
EP2172118A3 (fr) 2011-09-07
WO2007146318A9 (fr) 2008-03-13
WO2007146318A3 (fr) 2009-04-09
US20080213433A1 (en) 2008-09-04

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